This invention relates to novel pyrazole sulfonylureas which are expected to be useful as pre- and post-emergence herbicides. In addition, some of the sulfonylureas should show selective herbicidal activity.
Herbicidal sulfonylureas are generally disclosed in U.S. Pat. Nos. 4,127,405 and 4,167,719.
U.S. Pat. No. 486,042 discloses herbicidal imidazole and pyrazole sulfonylureas such as: ##STR1##
EP-A-79,683 discloses benzofuran sulfonylureas such as: ##STR2##
U.S. Pat. No. 533,341 teaches sulfonylureas such as: ##STR3##
EP-A-87,780 (published 9/7/83) filed by Nissan Chemical Industries teaches pyrazole sulfonylureas of the following general formula. ##STR4## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
B and C are independently H, halogen, C.sub.1 -C.sub.8 alkyl, CO.sub.2 R, SO.sub.2 NR.sub.4 R.sub.5, etc. PA0 D is H or C.sub.1 -C.sub.8 alkyl; PA0 X and Y are independently H, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, etc.; and PA0 Z is C--R.sub.8 or N. PA0 R.sub.3 is H, C.sub.1 -C.sub.3 alkyl or CHF.sub.2 ; PA0 R.sub.4 is H, Cl or CH.sub.3 ; PA0 R.sub.5 is H, Cl or CH.sub.3 ; PA0 R.sub.6 is H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.7 is H or CH.sub.3 ; PA0 n is 0 or 1; PA0 Q is O, S or NCH.sub.3 ; PA0 Q.sub.1 is O, S or SO.sub.2 ; PA0 A is ##STR8## X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, F, Cl, Br, CF.sub.3, OCF.sub.2 H or CFH.sub.2 ; PA0 Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, SeCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, CR.sub.8 (WCH.sub.3).sub.2, ##STR9## or CR.sub.8 (WCH.sub.2 CH.sub.3).sub.2 ; R.sub.8 is H or CH.sub.3 ; PA0 W is O or S; PA0 Z is CH or N; PA0 Y.sub.1 is CH.sub.2 or O; PA0 X.sub.1 is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 H; PA0 Y.sub.2 is H or CH.sub.3 ; PA0 X.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA0 Y.sub.3 is OCH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA0 (1) Compounds of Formula I where A is A-1 and R is H. PA0 (2) Compounds of Preferred 1 where X is CH.sub.3, OCH.sub.3 or Cl and Y is C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CF.sub.3, OCH.sub.2 CF.sub.3, CH(OCH.sub.3).sub.2, or cyclopropyl. PA0 (3) Compounds of Preferred 2 where L is L-1, L-2, L-3, L-4, L-5, L-6, L-7, L-8, L-9 or L-10. PA0 (4) Compounds of Preferred 3 where R.sub.1 is H or C.sub.1 -C.sub.3 alkyl, R.sub.2 is H or CH.sub.3, R.sub.3 is CH.sub.3, R.sub.4 is H or CH.sub.3, R.sub.5 is H or CH.sub.3, R.sub.6 is H or CH.sub.3, R.sub.7 is H and Q is O. PA0 (5) Compounds of Preferred 4 where L is L-1. PA0 (6) Compounds of Preferred 4 where L is L-2. PA0 (7) Compounds of Preferred 4 where L is L-3. PA0 (8) Compounds of Preferred 4 where L is L-4. PA0 (9) Compounds of Preferred 4 where L is L-5. PA0 (10) Compounds of Preferred 4 where L is L-6. PA0 (11) Compounds of Preferred 4 where L is L-7. PA0 (12) Compounds of Preferred 4 where L is L-8. PA0 (13) Compounds of Preferred 4 where L is L-9. PA0 (14) Compounds of Preferred 4 where L is L-10. PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4,6-dihydro-2-methyl-4-oxo- 2 H-furo[3,4-c]pyrazole-3-sulfonamide; and PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,4,6,7-tetrahydro-2-methyl - 4-oxopyrano[4,3-c]pyrazole-3-sulfonamide.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat and the like. The current population explosion and the concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of a valuable crop by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.